58993-81-0

Upstream product

• 2801-68-5 2,5-dimethoxyphenylisopropylamine 
• 609771-70-2 (2S)-1-(2,5-dimethoxyphenyl)-2-propyl tosylate 
• 609771-69-9 (2S)-1-(2,5-dimethoxyphenyl)-2-propanol 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 609771-72-4 (2R)-1-(2,5-dimethoxyphenyl)-2-propyl azide 

Downstream Products

• 43061-15-0 (-)-Brolamfetamine 

Relevant academic research and scientific papers

Stereospecific synthesis of amphetamines

Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine.

Asymmetric synthesis of phenylisopropylamines

The synthesis of enantiomers of a series of methoxy- and alkyl- substituted phenylisopropylamines is described. The synthesis comprises reducing the imines, formed by the reaction of appropriate phenylacetones with either (+)- or (-)-α-methylbenzylamine, by low-pressure reduction techniques, and subsequently subjecting the optically active N-(α-phenethyl)phenylisopropylamine derivative to hydrogenolysis. The hydrogenolysis products are characterized by enantiomeric purities in the range of 96 - 99%. Yields of products are approximately 60%.